jmduke

Joined 15 years ago

Karma
19,865
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1,843
Member since
Dec 31
I run Buttondown (https://buttondown.com).

ex-Stripe, ex-Amazon.

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https://twitter.com/jmduke https://jmduke.com [email protected]

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Recent submissions

Comment · 5 months ago
With all due respect to Kevin Kelly (who has lived a life worthy of the aphorisms he writes!), I prefer the guidance of George Saunders (via Lincoln in the Bardo):

> Please do not misunderstand. We had been mothers, fathers. Had been husbands of many years, men of import, who had come here, that first day, accompanied by crowds so vast and sorrowful that, surging forward to hear the oration, they had damaged fences beyond repair. Had been young wives, diverted here during childbirth, our gentle qualities stripped from us by the naked pain of that circumstance, who left behind husbands so enamored of us, so tormented by the horror of those last moments (the notion that we had gone down that awful black hole pain-sundered from ourselves) that they had never loved again. Had been bulky men, quietly content, who, in our first youth, had come to grasp our own unremarkableness and had, cheerfully (as if bemusedly accepting a heavy burden), shifted our life’s focus; if we would not be great, we would be useful; would be rich, and kind, and thereby able to effect good: smiling, hands in pockets, watching the world we had subtly improved walking past (this empty dowry filled; that education secretly funded). Had been affable, joking servants, of whom our masters had grown fond for the cheering words we managed as they launched forth on days full of import. Had been grandmothers, tolerant and frank, recipients of certain dark secrets,who, by the quality of their unjudging listening, granted tacit forgiveness, and thus let in the sun. What I mean to say is, we had been considerable. Had been loved. Not lonely, not lost, not freakish, but wise, each in his or her own way. Our departures caused pain. Those who had loved us sat upon their beds, heads in hand; lowered their faces to tabletops, making animal noises. We had been loved, I say, and remembering us, even many years later, people would smile, briefly gladdened at the memory.

Comment · 1 year ago
It's an interesting question! To me, an (or perhaps _the_) obvious threshold is once the emails become automated.
Comment · 1 year ago
I think the definition of spam necessitates some level of bulk sending, and I struggle to consider ~fifty emails over the course of two or three years "bulk".
Comment · 1 year ago
The vast majority of commenters are being negative about this essay, and I agree with the negativity, because _automated cold emails_ are awful. (As are sequences, and mail merges.)

However!

_Bespoke cold emails_ are I think, a dying/lost art. I want to give an example of two cold emails that I (manually!) send a few times a month. (I run Buttondown, which is an email SaaS — think similar to Mailchimp, ConvertKit, etc.)

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The first is to folks who have the following criteria:

1. they hit the front page of HN

2. they have a personal blog that isn't tied to a platform (e.g. they're using jekyll or something similar)

3. they have RSS enabled

4. they do _not_ collect email addresses

The thrust of the email is this:

``` Hi! I'm the founder of Buttondown, a newsletter tool for technical blogs. I'm reaching out because:

1. You just hit HN front page! (Congrats and/or my condolences.) 2. You've got an RSS feed but are not capturing emails.

My proposal: I set you up with a free (for life!) Buttondown account seeded with your blog's RSS feed. All you do is drop in a form tag or an iFrame in your blog and folks can sign up with their email address and get an email whenever you publish something new. I can handle the setup and then hand it off to you for perpetuity.

If this is something you're at all interested in, please let me know! (There's no catch, and this isn't an automated email, so please — I'd love to hear why not, even if the answer is simply "shove off, I don't care about collecting an audience, Twitter and Mastodon are sufficient"). ```

(I tweak the language based on their own voice, mention what in particular I like about their blog, etc.)

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The second is to folks who fit the following criteria:

1. they're a technical newsletter publishing programming-related content

2. they're using a platform that I know to be particularly expensive relative to me (Mailchimp, ActiveCampaign are the two big culprits here)

``` hi there! I run Buttondown — you may have heard of us, we're used by RELEVANT_CUSTOMER_1 and RELEVANT_CUSTOMER_2. I see you're using OTHER_PLATFORM; is there anything I could do to get you to switch to [us](https://buttondown.com/pricing?count=7500)

(btw, this is a real email, not a marketing campaign. it's still early days for us, so tbh you telling me why you're _not_ interested is just as valuable as getting to call you a customer :) ```

Small sample size for both genres — I've probably sent them a total of ~fifty times — but the response rate is around 80% and conversion rate (though granted for the first genre "conversion" is more of a second-order effect, since I'm offering them a free account!) is ~25%.

I say all of this because, as someone who a priori _hated_ outbound and "sales stuff", I learned that at least for me and my business both the most palatable _and_ most effective method was just being earnest and helpful. It has been the single most useful non-technical skill I've gained over the past few years.

Comment · 2 years ago
Comment · 2 years ago
This dovetails with my own experience more or less exactly: when I launched my company, it was easy to throw everything on Heroku, and to their credit and detriment it was also fairly easy to move pretty much everything _off_ of Heroku (RDS for a database, RedisLabs for, well, Redis, and so on.)

Back in 2021 (https://news.ycombinator.com/item?id=29648325, https://news.ycombinator.com/item?id=30177907) and 2022 (https://news.ycombinator.com/item?id=32608734) Heroku went from "well this is costing enough that it probably makes sense to divest at some point and save the $X00/mo" to "Heroku is now the biggest systemic risk to uptime that I have", and it felt _very_ high-priority to get off of them and onto someone else.

Two years later, though... the inclination has ebbed. Heroku hasn't shipped anything meaningful for my use case in the past 24 months, but also they have been fairly stable. I'm sure I will migrate off of them onto something else in the fullness of time, but it would take a pretty severe precipitating event.

Comment · 2 years ago
Comment · 2 years ago
The only through-line for the author's definition of "bogus" (AI generated content; identity performance; rejection of canon) appears to me "cannot be situated in the culture of a few decades ago."

To pick on one example: he writes of the linked NYT essay:

> Is greatness overrated? What’s next—Is disease the new health? Is losing the new winning? Is stupid the new smart?

At risk of sounding uncharitable, this is the kind of reaction one might have to the essay if they read the title and skipped the content. The author is specfically talking about the idea of the Nobel canon and its orthogonality to other reasons you might want to read an author. (I don't think it's a particularly good essay, but it's certainly not saying "bad stuff is good, actually"!)

Comment · 2 years ago
Yup, absolutely — you see a lot of the larger brokers do some genre of lease-to-own program (pay us the purchase price plus a near-usurious APY over 24mos and at the end, you can keep the domain.)

My margins are solid and there aren't a lot of competing opportunities to deploy capital besides pulling forward cloud costs or hiring folks (which is a very different value prop altogether), so reasoning about the lump sum was pretty easy, but you're definitely right in that objectively speaking I should have just gotten a line of credit and amortized it that way.

Comment · 2 years ago
Honestly, as long as you don't call it "Buttdown"... (this happens more than you'd think.)
Comment · 2 years ago
And my old blog domain to boot! Exactly what I meant by "The hardest part of the process was the stuff you can't grep for..."

(T/Y — fixed.)

Comment · 2 years ago
Definitely not _necessary_ — I was more or less resigned to not having the domain, since the sticker price was $170K and my mental "is this _really_ worth it?" number was high five figures.

As for why important: a melange of reasons. I had heard a _lot_ from customers and prospects that they couldn't find the site because they searched for/navigated to buttondown.com; I was faintly worried about SEO/brand impact from using a vanity TLD like `.email`; I was faintly worried about a more well-financed competitor buying it and redirecting to their own property; there are a very real number of legacy pieces of software that do not _accept_ `buttondown.email` as a valid domain, which is important when you're dealing with UGC.

(When I was debating what a reasonable purchase price might be, the framing that helped me make a decision was: "if this helps my overall conversion funnel grow by 2% in perpetuity, is it worth it?", and that answer was yes. Time will tell, of course, to see where that number actually lands!)

Comment · 2 years ago
Comment · 2 years ago
Author here! Happy to answer any questions folks have.

(I would also be remiss if I didn't say that I am grateful to HN for introducing me to what was called microISVs a decade ago, "indie hacking" five years ago, and now I suppose is mostly called "building in public" / "lifestyle businesses". I was inspired to start Buttondown in no small part due to reading about Candy Japan, Appointment Reminder, et al, and learning that there was a different yet equally valid path for growing a SaaS)

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